DL 2816 then BR 643 at O'Hare
Boston → Chicago → Anchorage
Timetable, Chicago time
14:02DL 2816 from Boston at the gate
11:55BR 643 to Anchorage leaves the gate
21 h 53 apart on the timetable, overnight
BR 643 leaves 21 h 53 after DL 2816 arrives on the timetable: more than half a day, so not a connection we count.